Reaktion #75568

Reaktionsgleichung

3-chloroperbenzoic acid

sodium hydrogen carbonate

dichloroketene

diazomethane

trichloroacetyl chloride

cyclobutanone

dichlorocyclobutanone

→

cyclopentanone

( f )

dichlorocyclobutanone

Lösungsmittel

dichloromethane

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigecan be obtained
2. 2
   Sonstigeis preferably 10 to 50° C
3. 3
   Sonstigecan be obtained
4. 4
   Sonstigeis preferably in the range of from room temperature to 40° C

Vorschrift

The compound (b) is reacted with trichloroacetyl chloride in a solvent such as diethyl ether, dimethoxyethane or tetrahydrofuran to give the dichlorocyclobutanone compound (f) (Alternatively, when it is reacted with diacetyl chloride, a monochloro-compound is obtained. The monochloro-compound can also be obtained by reacting with trichloroacetyl chloride, followed by treating with acetic acid.), and then the product is treated with a reducing agent such as zinc dust, whereby the cyclobutanone compound represented by the formula (g) can be obtained. The reaction temperature is preferably 10 to 50° C. When the compound (g) is treated with a peroxide such as 3-chloroperbenzoic acid in the presence of sodium hydrogen carbonate in a solvent such as dichloromethane, the lactone compound represented by the formula (h) can be obtained. The reaction temperature is preferably in the range of from room temperature to 40° C. When the compound (b) is treated with dichloroketene and diazomethane, a cyclopentanone compound in the formula (f) is obtained, and when the compound (g) is treated with diazomethane, a cyclopentanone compound in formula (g) is obtained. When the cyclopentanone compound is further treated with diazomethane, a cyclohexanone compound is obtained.

Quelle